5-ethyl-6-[5-(3-cyano-4-isopropoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: 5-ethyl-6-[5-(3-cyano-4-isopropoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 1258856-72-2
• Molecular Formula: C₂₃H₂₄N₄OS
• Molecular Weight: 404.536
• Mol file: 1258856-72-2.mol

Synonyms:5-ethyl-6-[5-(3-cyano-4-isopropoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-1,2,3,4-tetrahydroisoquinoline

Chemical Property of 5-ethyl-6-[5-(3-cyano-4-isopropoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-ethyl-6-[5-(3-cyano-4-isopropoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-1,2,3,4-tetrahydroisoquinoline

There total 14 articles about 5-ethyl-6-[5-(3-cyano-4-isopropoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-1,2,3,4-tetrahydroisoquinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5-(5-bromo-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)oxy]-benzonitrile + 1-[5-ethyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoroethanone (1258440-82-2) → 5-ethyl-6-[5-(3-cyano-4-isopropoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-1,2,3,4-tetrahydroisoquinoline (1258856-72-2)

Guidance literature:

With sodium carbonate; In 1,2-dimethoxyethane; water; Reflux; Inert atmosphere;

Reference yield:

1,3-dibromobenzene (108-36-1) → 5-ethyl-6-[5-(3-cyano-4-isopropoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-1,2,3,4-tetrahydroisoquinoline (1258856-72-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / -78 - -70 °C / Inert atmosphere

1.2: 0.33 h

2.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

2.2: 2 h

3.1: ammonium acetate / 3 h / Reflux

4.1: chloro-trimethyl-silane; lithium borohydride / tetrahydrofuran / 0 - 20 °C / Reflux

5.1: triethylamine / dichloromethane / 0 - 20 °C

6.1: sulfuric acid; acetic acid / 4 h / 70 °C

7.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 10 h / Reflux

8.1: sodium carbonate / 1,2-dimethoxyethane; water / Reflux; Inert atmosphere

With lithium borohydride; n-butyllithium; chloro-trimethyl-silane; sulfuric acid; ammonium acetate; potassium acetate; sodium carbonate; acetic acid; triethylamine; diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; hexane; dichloromethane; water;

Reference yield:

salicylonitrile (611-20-1) → 5-ethyl-6-[5-(3-cyano-4-isopropoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-1,2,3,4-tetrahydroisoquinoline (1258856-72-2)

Guidance literature:

Multi-step reaction with 5 steps

1: trifluorormethanesulfonic acid; N-iodo-succinimide / acetonitrile / 0 - 20 °C

2: potassium carbonate / acetonitrile / Reflux

3: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 90 °C / Inert atmosphere

4: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / Reflux; Inert atmosphere

5: sodium carbonate / 1,2-dimethoxyethane; water / Reflux; Inert atmosphere

With N-iodo-succinimide; trifluorormethanesulfonic acid; potassium acetate; sodium carbonate; potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; 1,2-dimethoxyethane; water; acetonitrile;

upstream raw materials:

1-[5-ethyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoroethanone

1,3-dibromobenzene

salicylonitrile

3-cyano-4-isopropoxybenzoic acid